JP2010513397A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010513397A5 JP2010513397A5 JP2009542043A JP2009542043A JP2010513397A5 JP 2010513397 A5 JP2010513397 A5 JP 2010513397A5 JP 2009542043 A JP2009542043 A JP 2009542043A JP 2009542043 A JP2009542043 A JP 2009542043A JP 2010513397 A5 JP2010513397 A5 JP 2010513397A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazol
- phenyl
- indol
- chloro
- oxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 trifluoromethoxy , Difluoromethoxy Chemical group 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- QFOCXKVUZZDCDL-UHFFFAOYSA-N 3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCC(O)=O)C3=CC=2)=NO1 QFOCXKVUZZDCDL-UHFFFAOYSA-N 0.000 claims 2
- HLDBXISXBVARTO-UHFFFAOYSA-N 4-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCCC(O)=O)C3=CC=2)=NO1 HLDBXISXBVARTO-UHFFFAOYSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000001419 dependent Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 150000003235 pyrrolidines Chemical class 0.000 claims 2
- RYCURDRPWHCXQR-AWEZNQCLSA-N (2S)-3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]-2-methylpropanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(C[C@H](C)C(O)=O)C3=CC=2)=NO1 RYCURDRPWHCXQR-AWEZNQCLSA-N 0.000 claims 1
- JDKAJAKVJGLQIO-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CC(C)(C)C(O)=O)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 JDKAJAKVJGLQIO-UHFFFAOYSA-N 0.000 claims 1
- QDKQSBXYKYZLMW-UHFFFAOYSA-N 2-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CC(O)=O)C=3C=CC=2)=NO1 QDKQSBXYKYZLMW-UHFFFAOYSA-N 0.000 claims 1
- JNCSFNYUKWYUDF-UHFFFAOYSA-N 2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CC(O)=O)C=3C=CC=2)=NO1 JNCSFNYUKWYUDF-UHFFFAOYSA-N 0.000 claims 1
- JQVFIRYJMBZLQN-UHFFFAOYSA-N 2-[5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C=1C=C2N(CC(=O)O)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 JQVFIRYJMBZLQN-UHFFFAOYSA-N 0.000 claims 1
- GZCAFNMJWRFCPB-UHFFFAOYSA-N 3-[3-bromo-5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C(Br)=CN(CCC(O)=O)C3=CC=2)=NO1 GZCAFNMJWRFCPB-UHFFFAOYSA-N 0.000 claims 1
- IHFJSTWVWRLHRP-UHFFFAOYSA-N 3-[3-chloro-4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=C(Cl)C2=C1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 IHFJSTWVWRLHRP-UHFFFAOYSA-N 0.000 claims 1
- ATRHHCBTXLJODU-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-chloro-4-ethoxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OCC)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 ATRHHCBTXLJODU-UHFFFAOYSA-N 0.000 claims 1
- NSXLYJQAZFEOGH-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 NSXLYJQAZFEOGH-UHFFFAOYSA-N 0.000 claims 1
- KOHQHMAPKUTNNE-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 KOHQHMAPKUTNNE-UHFFFAOYSA-N 0.000 claims 1
- YEWFYEAYIRWLBU-UHFFFAOYSA-N 3-[3-chloro-5-[5-(4-chloro-3-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC(C=2ON=C(N=2)C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=C1 YEWFYEAYIRWLBU-UHFFFAOYSA-N 0.000 claims 1
- VWGIWRCFAHCBKK-UHFFFAOYSA-N 3-[3-chloro-5-[5-(4-methoxy-3-phenylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=2ON=C(N=2)C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)C=C1C1=CC=CC=C1 VWGIWRCFAHCBKK-UHFFFAOYSA-N 0.000 claims 1
- XHSNHDLFBNSHHH-UHFFFAOYSA-N 3-[3-chloro-5-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C1=CC=C(OC(F)(F)F)C(Cl)=C1 XHSNHDLFBNSHHH-UHFFFAOYSA-N 0.000 claims 1
- SJDIWNCKZJNHPE-UHFFFAOYSA-N 3-[3-chloro-5-[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 SJDIWNCKZJNHPE-UHFFFAOYSA-N 0.000 claims 1
- YOCISYLTMKQWMT-UHFFFAOYSA-N 3-[3-chloro-5-[5-[4-nitro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 YOCISYLTMKQWMT-UHFFFAOYSA-N 0.000 claims 1
- CDRBYCWJUGAZCB-UHFFFAOYSA-N 3-[3-chloro-5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 CDRBYCWJUGAZCB-UHFFFAOYSA-N 0.000 claims 1
- JWIKJHGBIFHLPM-UHFFFAOYSA-N 3-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 JWIKJHGBIFHLPM-UHFFFAOYSA-N 0.000 claims 1
- XAJVGJHOAIETSC-UHFFFAOYSA-N 3-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 XAJVGJHOAIETSC-UHFFFAOYSA-N 0.000 claims 1
- ZDNCNPFZPVFQLU-UHFFFAOYSA-N 3-[4-[5-(3-ethyl-4-piperidin-1-ylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound CCC1=CC(C=2ON=C(N=2)C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=CC=C1N1CCCCC1 ZDNCNPFZPVFQLU-UHFFFAOYSA-N 0.000 claims 1
- ZRMYIOJUUABNBB-UHFFFAOYSA-N 3-[4-[5-(4-cyclohexyl-3-ethylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound CCC1=CC(C=2ON=C(N=2)C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=CC=C1C1CCCCC1 ZRMYIOJUUABNBB-UHFFFAOYSA-N 0.000 claims 1
- FLERAFQOOGRXHE-UHFFFAOYSA-N 3-[4-[5-(5-chloro-6-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=NC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 FLERAFQOOGRXHE-UHFFFAOYSA-N 0.000 claims 1
- QIHAASGINXICIX-UHFFFAOYSA-N 3-[4-[5-[4-(2-fluorophenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1F QIHAASGINXICIX-UHFFFAOYSA-N 0.000 claims 1
- BGXPNVXUXLUWGQ-UHFFFAOYSA-N 3-[4-[5-[4-(2-methylpropyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(CC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 BGXPNVXUXLUWGQ-UHFFFAOYSA-N 0.000 claims 1
- FONMSGPEBHUUIV-UHFFFAOYSA-N 3-[4-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1CCCCC1 FONMSGPEBHUUIV-UHFFFAOYSA-N 0.000 claims 1
- NORSCQNGKKVMIO-UHFFFAOYSA-N 3-[4-[5-[4-phenyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 NORSCQNGKKVMIO-UHFFFAOYSA-N 0.000 claims 1
- GVFAFIKUOWUAIQ-UHFFFAOYSA-N 3-[4-[5-[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 GVFAFIKUOWUAIQ-UHFFFAOYSA-N 0.000 claims 1
- HCWIAVVSUBERJZ-UHFFFAOYSA-N 3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]-2,2,3-trifluoropropanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(C3=CC=2)C(F)C(F)(F)C(O)=O)=NO1 HCWIAVVSUBERJZ-UHFFFAOYSA-N 0.000 claims 1
- JXFAYGCVJMEDKI-UHFFFAOYSA-N 3-[5-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCC(O)=O)C3=CC=2)=NO1 JXFAYGCVJMEDKI-UHFFFAOYSA-N 0.000 claims 1
- RAXQVKOQRHWHOU-UHFFFAOYSA-N 3-[5-[5-[3-phenyl-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=CC2=CC=1C(N=1)=NOC=1C(C=1)=CC=C(C(F)(F)F)C=1C1=CC=CC=C1 RAXQVKOQRHWHOU-UHFFFAOYSA-N 0.000 claims 1
- WHHGUZLUCIYBPL-UHFFFAOYSA-N 4-[4-[5-(3-bromo-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Br)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 WHHGUZLUCIYBPL-UHFFFAOYSA-N 0.000 claims 1
- SKMHVWFGAFXNPS-UHFFFAOYSA-N 4-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 SKMHVWFGAFXNPS-UHFFFAOYSA-N 0.000 claims 1
- APHXDFHTQCIQBC-UHFFFAOYSA-N 4-[4-[5-(3-cyano-4-phenylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=CC=C2N(CCCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C#N)=CC=C1C1=CC=CC=C1 APHXDFHTQCIQBC-UHFFFAOYSA-N 0.000 claims 1
- UHURKDFLIMINLN-UHFFFAOYSA-N 4-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 UHURKDFLIMINLN-UHFFFAOYSA-N 0.000 claims 1
- NFIGDBFIDKDNIG-UHFFFAOYSA-N 4-[4-[5-(5-chloro-6-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=NC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 NFIGDBFIDKDNIG-UHFFFAOYSA-N 0.000 claims 1
- ZOAACYIIORBWGO-UHFFFAOYSA-N 4-[4-[5-[3-chloro-4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(CC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 ZOAACYIIORBWGO-UHFFFAOYSA-N 0.000 claims 1
- GJFQCFCPADTPMV-UHFFFAOYSA-N 4-[4-[5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(CC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 GJFQCFCPADTPMV-UHFFFAOYSA-N 0.000 claims 1
- LWXBLIIYLSYXCB-MRXNPFEDSA-N 4-[4-[5-[4-[(2R)-butan-2-yl]oxy-3-cyanophenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(O[C@H](C)CC)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 LWXBLIIYLSYXCB-MRXNPFEDSA-N 0.000 claims 1
- LWXBLIIYLSYXCB-INIZCTEOSA-N 4-[4-[5-[4-[(2S)-butan-2-yl]oxy-3-cyanophenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(O[C@@H](C)CC)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 LWXBLIIYLSYXCB-INIZCTEOSA-N 0.000 claims 1
- LMXLJFSUXSWIFZ-UHFFFAOYSA-N 4-[4-[5-[4-phenyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=CC=C2N(CCCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 LMXLJFSUXSWIFZ-UHFFFAOYSA-N 0.000 claims 1
- VXNIDFMYHIAKQT-UHFFFAOYSA-N 5-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCCCC(O)=O)C3=CC=2)=NO1 VXNIDFMYHIAKQT-UHFFFAOYSA-N 0.000 claims 1
- 206010003246 Arthritis Diseases 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 206010003816 Autoimmune disease Diseases 0.000 claims 1
- XNSGYCLMPVYDMN-UHFFFAOYSA-N C(#N)C1N(CCCC1)OC(F)(F)F Chemical compound C(#N)C1N(CCCC1)OC(F)(F)F XNSGYCLMPVYDMN-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010011401 Crohn's disease Diseases 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- 101710031679 HEXIM1 Proteins 0.000 claims 1
- 206010021972 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010027476 Metastasis Diseases 0.000 claims 1
- 206010029331 Neuropathy peripheral Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 102100014085 S1PR1 Human genes 0.000 claims 1
- 208000001756 Virus Disease Diseases 0.000 claims 1
- 230000001154 acute Effects 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 201000009596 autoimmune hypersensitivity disease Diseases 0.000 claims 1
- 230000001684 chronic Effects 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000002757 inflammatory Effects 0.000 claims 1
- 200000000018 inflammatory disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated Effects 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 201000004681 psoriasis Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 201000006704 ulcerative colitis Diseases 0.000 claims 1
- 201000011528 vascular disease Diseases 0.000 claims 1
Claims (7)
R5およびR6のうち一方は、水素またはR2であり、他方は、(a):
Aは、フェニルまたは5員もしくは6員ヘテロアリール環であり;
R1は、水素であるか、またはハロゲン、C(1-6)アルキル、C(3-6)シクロアルキル、C(1-6)アルコキシ、C(3-6)シクロアルキルオキシ、トリフルオロメトキシ、ジフルオロメトキシ、トリフルオロメチル、シアノ、ニトロ、置換されていてもよいピペリジン、置換されていてもよいピロリジン、置換されていてもよいフェニルおよび置換されていてもよい5員または6員ヘテロアリール環から独立して選択される3個までの置換基であり;
R1がフェニル、ピペリジン、ピロリジンまたは5員もしくは6員ヘテロアリール環である場合、それは、ハロゲン、C(1-6)アルキル、C(1-6)アルコキシ、トリフルオロメトキシ、ジフルオロメトキシ、C3-6シクロアルキル、トリフルオロメチルおよびシアノから選択される3個までの置換基によって置換されていてよく;
R2は、水素であるか、または、ハロゲン、C(1-4)アルキル、C(1-4)アルコキシ、トリフルオロメトキシ、ジフルオロメトキシ、トリフルオロメチルおよびシアノから独立して選択される3個までの置換基であり;
R7は、水素またはハロゲンであり;
Zは、NまたはOによって中断されていてもよいC(1-4)アルキルであり、ハロゲンまたはメチルによって置換されていてもよい]
で示される化合物またはその医薬上許容される塩。 Formula (I):
One of R 5 and R 6 is hydrogen or R 2 and the other is (a):
A is phenyl or a 5 or 6 membered heteroaryl ring;
R 1 is hydrogen or halogen, C (1-6) alkyl, C (3-6) cycloalkyl, C (1-6) alkoxy, C (3-6) cycloalkyloxy, trifluoromethoxy , Difluoromethoxy, trifluoromethyl, cyano, nitro, optionally substituted piperidine, optionally substituted pyrrolidine, optionally substituted phenyl and optionally substituted 5 or 6 membered heteroaryl ring Up to three substituents independently selected from
When R 1 is phenyl, piperidine, pyrrolidine or a 5- or 6-membered heteroaryl ring, it is halogen, C (1-6) alkyl, C (1-6) alkoxy, trifluoromethoxy, difluoromethoxy, C 3 Optionally substituted by up to 3 substituents selected from -6 cycloalkyl, trifluoromethyl and cyano;
R 2 is hydrogen or three independently selected from halogen, C (1-4) alkyl, C (1-4) alkoxy, trifluoromethoxy, difluoromethoxy, trifluoromethyl and cyano Up to substituents;
R 7 is hydrogen or halogen;
Z is C (1-4) alkyl optionally interrupted by N or O, optionally substituted by halogen or methyl]
Or a pharmaceutically acceptable salt thereof.
Aがチエニル、ピリジルまたはフェニルである;および/または
R1が、ハロゲン、C1-6アルコキシ、またはトリフルオロメチル、置換されていてもよいフェニル、置換されていてもよいシクロヘキシル、シアノ、トリフルオロメトキシ、置換されていてもよいピペリジン、置換されていてもよいピロリジン、C1-6アルキルおよびNO2から選択される3個までの置換基である;および/または
R2が水素である;および/または
R7が水素またはハロゲンである;および/または
ZがNまたはOによって中断されていてもよいC(1-4)アルキルであり、フルオロまたはメチルによって置換されていてもよい、
式(I)で示される化合物またはその医薬上許容される塩。 R 5 is hydrogen and R 6 is (a); and / or A is thienyl, pyridyl or phenyl; and / or R 1 is halogen, C 1-6 alkoxy, or trifluoromethyl, substituted It is phenyl optionally, cyclohexyl optionally substituted, cyano, trifluoromethoxy, piperidine which may be substituted, an optionally substituted pyrrolidine, 3 is selected from C 1-6 alkyl and NO 2 And / or R 2 is hydrogen; and / or R 7 is hydrogen or halogen; and / or Z may be interrupted by N or O (1-4 ) Alkyl, optionally substituted by fluoro or methyl,
A compound represented by formula (I) or a pharmaceutically acceptable salt thereof.
3−(5−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−[3−クロロ−5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−(3−クロロ−5−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(4−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−[4−(5−{3−クロロ−4−[(トリフルオロメチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−[4−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−[4−(5−{5−クロロ−6−[(1−メチルエチル)オキシ]−3−ピリジニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
(5−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)酢酸;
3−[3−ブロモ−5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
5−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ペンタン酸;
4−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
4−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
(2S)−3−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]−2−メチルプロパン酸;
2,2−ジメチル−3−(5−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−[5−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]−2,2,3−トリフルオロプロパン酸;
4−[4−(5−{3−シアノ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
3−[5−(5−{3−シアノ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−[4−(5−{3−シアノ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−(4−{5−[2−(トリフルオロメチル)−4−ビフェニリル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(4−{5−[4−シクロヘキシル−3−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(4−{5−[4−[(1−メチルエチル)オキシ]−3−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
[4−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]酢酸;
[4−(5−{3−シアノ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]酢酸;
3−(4−{5−[2'−フルオロ−2−(トリフルオロメチル)−4−ビフェニリル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
4−[4−(5−{3−クロロ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
4−[4−(5−{3−クロロ−4−[(トリフルオロメチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
4−[4−(5−{5−クロロ−6−[(1−メチルエチル)オキシ]−3−ピリジニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
4−(4−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)ブタン酸;
4−(4−{5−[2−(トリフルオロメチル)−4−ビフェニリル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)ブタン酸;
3−(4−{5−[4−(メチルオキシ)−3−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
4−{4−[5−(3−シアノ−4−{[(1R)−1−メチルプロピル]オキシ}フェニル)−1,2,4−オキサジアゾール−3−イル]−1H−インドール−1−イル}ブタン酸;
4−{4−[5−(3−シアノ−4−{[(1S)−1−メチルプロピル]オキシ}フェニル)−1,2,4−オキサジアゾール−3−イル]−1H−インドール−1−イル}ブタン酸;
3−(4−{5−[3−エチル−4−(1−ピペリジニル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−{4−[5−(4−シクロヘキシル−3−エチルフェニル)−1,2,4−オキサジアゾール−3−イル]−1H−インドール−1−イル}プロパン酸;
3−(4−{5−[5−クロロ−6−(1−ピロリジニル)−3−ピリジニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
4−[4−(5−{3−ブロモ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]ブタン酸;
4−(4−{5−[3−クロロ−4−(2−メチルプロピル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)ブタン酸;
3−(4−{5−[4−(2−メチルプロピル)−3−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
4−(4−{5−[3−シアノ−4−(2−メチルプロピル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)ブタン酸;
4−{4−[5−(2−シアノ−4−ビフェニリル)−1,2,4−オキサジアゾール−3−イル]−1H−インドール−1−イル}ブタン酸;
3−(3−クロロ−4−{5−[4−フェニル−5−(トリフルオロメチル)−2−チエニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−[3−クロロ−5−(5−{3−クロロ−4−[(トリフルオロメチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−(3−クロロ−5−{5−[3−クロロ−4−(プロピルオキシ)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(3−クロロ−5−{5−[3−クロロ−4−(メチルオキシ)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(3−クロロ−5−{5−[4−(メチルオキシ)−3−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(3−クロロ−5−{5−[3−クロロ−4−(エチルオキシ)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−[3−クロロ−5−(5−{3−シアノ−4−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−(3−クロロ−5−{5−[4−ニトロ−3−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−[3−クロロ−5−(5−{4−クロロ−3−[(1−メチルエチル)オキシ]フェニル}−1,2,4−オキサジアゾール−3−イル)−1H−インドール−1−イル]プロパン酸;
3−(3−クロロ−5−{5−[6−(メチルオキシ)−3−ビフェニリル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
3−(5−{5−[6−(トリフルオロメチル)−3−ビフェニリル]−1,2,4−オキサジアゾール−3−イル}−1H−インドール−1−イル)プロパン酸;
およびそれらの医薬上許容される塩。 A compound selected from:
3- (5- {5- [4-Phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propane acid;
3- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Propanoic acid;
3- [3-Chloro-5- (5- {3-chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indole- 1-yl] propanoic acid;
3- (3-Chloro-5- {5- [4-phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indole-1 -Yl) propanoic acid;
3- (4- {5- [4-Phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propane acid;
3- [4- (5- {3-Chloro-4-[(trifluoromethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] propane acid;
3- [4- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Propanoic acid;
3- [4- (5- {5-Chloro-6-[(1-methylethyl) oxy] -3-pyridinyl} -1,2,4-oxadiazol-3-yl) -1H-indole-1 -Yl] propanoic acid;
3- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Propanoic acid;
(5- {5- [4-Phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) acetic acid;
3- [3-Bromo-5- (5- {3-chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indole- 1-yl] propanoic acid;
5- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Pentanoic acid;
4- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Butanoic acid;
4- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Butanoic acid;
(2S) -3- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indole- 1-yl] -2-methylpropanoic acid;
2,2-Dimethyl-3- (5- {5- [4-phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indole -1-yl) propanoic acid;
3- [5- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] -2,2,3-trifluoropropanoic acid;
4- [4- (5- {3-cyano-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Butanoic acid;
3- [5- (5- {3-Cyano-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Propanoic acid;
3- [4- (5- {3-Cyano-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Propanoic acid;
3- (4- {5- [2- (trifluoromethyl) -4-biphenylyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propanoic acid;
3- (4- {5- [4-cyclohexyl-3- (trifluoromethyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propanoic acid;
3- (4- {5- [4-[(1-methylethyl) oxy] -3- (trifluoromethyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indole- 1-yl) propanoic acid;
[4- (5- {3-chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] acetic acid;
[4- (5- {3-cyano-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] acetic acid;
3- (4- {5- [2′-fluoro-2- (trifluoromethyl) -4-biphenylyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) Propanoic acid;
4- [4- (5- {3-Chloro-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Butanoic acid;
4- [4- (5- {3-Chloro-4-[(trifluoromethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] butane acid;
4- [4- (5- {5-Chloro-6-[(1-methylethyl) oxy] -3-pyridinyl} -1,2,4-oxadiazol-3-yl) -1H-indole-1 -Yl] butanoic acid;
4- (4- {5- [4-Phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) butane acid;
4- (4- {5- [2- (trifluoromethyl) -4-biphenylyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) butanoic acid;
3- (4- {5- [4- (Methyloxy) -3- (trifluoromethyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propane acid;
4- {4- [5- (3-cyano-4-{[(1R) -1-methylpropyl] oxy} phenyl) -1,2,4-oxadiazol-3-yl] -1H-indole- 1-yl} butanoic acid;
4- {4- [5- (3-cyano-4-{[(1S) -1-methylpropyl] oxy} phenyl) -1,2,4-oxadiazol-3-yl] -1H-indole- 1-yl} butanoic acid;
3- (4- {5- [3-ethyl-4- (1-piperidinyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propanoic acid;
3- {4- [5- (4-cyclohexyl-3-ethylphenyl) -1,2,4-oxadiazol-3-yl] -1H-indol-1-yl} propanoic acid;
3- (4- {5- [5-Chloro-6- (1-pyrrolidinyl) -3-pyridinyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propane acid;
4- [4- (5- {3-Bromo-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indol-1-yl] Butanoic acid;
4- (4- {5- [3-chloro-4- (2-methylpropyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) butanoic acid;
3- (4- {5- [4- (2-Methylpropyl) -3- (trifluoromethyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl ) Propanoic acid;
4- (4- {5- [3-cyano-4- (2-methylpropyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) butanoic acid;
4- {4- [5- (2-cyano-4-biphenylyl) -1,2,4-oxadiazol-3-yl] -1H-indol-1-yl} butanoic acid;
3- (3-Chloro-4- {5- [4-phenyl-5- (trifluoromethyl) -2-thienyl] -1,2,4-oxadiazol-3-yl} -1H-indole-1 -Yl) propanoic acid;
3- [3-Chloro-5- (5- {3-chloro-4-[(trifluoromethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indole-1 -Yl] propanoic acid;
3- (3-Chloro-5- {5- [3-chloro-4- (propyloxy) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propane acid;
3- (3-Chloro-5- {5- [3-chloro-4- (methyloxy) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propane acid;
3- (3-Chloro-5- {5- [4- (methyloxy) -3- (trifluoromethyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indole-1 -Yl) propanoic acid;
3- (3-Chloro-5- {5- [3-chloro-4- (ethyloxy) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propanoic acid ;
3- [3-Chloro-5- (5- {3-cyano-4-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indole- 1-yl] propanoic acid;
3- (3-Chloro-5- {5- [4-nitro-3- (trifluoromethyl) phenyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) Propanoic acid;
3- [3-Chloro-5- (5- {4-chloro-3-[(1-methylethyl) oxy] phenyl} -1,2,4-oxadiazol-3-yl) -1H-indole- 1-yl] propanoic acid;
3- (3-Chloro-5- {5- [6- (methyloxy) -3-biphenylyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propanoic acid ;
3- (5- {5- [6- (trifluoromethyl) -3-biphenylyl] -1,2,4-oxadiazol-3-yl} -1H-indol-1-yl) propanoic acid;
And their pharmaceutically acceptable salts.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0625647A GB0625647D0 (en) | 2006-12-21 | 2006-12-21 | Compounds |
GB0625647.3 | 2006-12-21 | ||
GB0707615.1 | 2007-04-19 | ||
GB0707615A GB0707615D0 (en) | 2007-04-19 | 2007-04-19 | Compounds |
PCT/EP2007/064185 WO2008074821A1 (en) | 2006-12-21 | 2007-12-19 | Indole derivatives as s1p1 receptor agonists |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010513397A JP2010513397A (en) | 2010-04-30 |
JP2010513397A5 true JP2010513397A5 (en) | 2010-08-19 |
JP5309034B2 JP5309034B2 (en) | 2013-10-09 |
Family
ID=39283563
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009542043A Expired - Fee Related JP5309034B2 (en) | 2006-12-21 | 2007-12-19 | Indole derivatives as S1P1 receptor agonists |
Country Status (33)
Country | Link |
---|---|
US (1) | US8101775B2 (en) |
EP (2) | EP2091949B1 (en) |
JP (1) | JP5309034B2 (en) |
KR (1) | KR101495927B1 (en) |
CN (1) | CN103012390B (en) |
AR (1) | AR064452A1 (en) |
AT (1) | ATE509927T1 (en) |
AU (1) | AU2007336224B2 (en) |
BR (1) | BRPI0721127A2 (en) |
CA (1) | CA2673468C (en) |
CL (1) | CL2007003755A1 (en) |
CR (2) | CR10922A (en) |
CY (2) | CY1111702T1 (en) |
DK (2) | DK2091949T3 (en) |
DO (1) | DOP2009000133A (en) |
EA (1) | EA017406B1 (en) |
ES (1) | ES2389879T3 (en) |
HK (2) | HK1140761A1 (en) |
HR (2) | HRP20110456T1 (en) |
IL (1) | IL199187A (en) |
JO (1) | JO2701B1 (en) |
MA (1) | MA30999B1 (en) |
MX (1) | MX2009006882A (en) |
MY (2) | MY156822A (en) |
NO (1) | NO20092385L (en) |
NZ (1) | NZ577387A (en) |
PE (2) | PE20121076A1 (en) |
PL (2) | PL2206710T3 (en) |
PT (2) | PT2206710E (en) |
SG (1) | SG177914A1 (en) |
SI (2) | SI2091949T1 (en) |
TW (1) | TWI393564B (en) |
WO (1) | WO2008074821A1 (en) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0709866B8 (en) | 2006-04-03 | 2021-05-25 | Astellas Pharma Inc | hetero compounds and pharmaceutical composition comprising said compounds |
JO2701B1 (en) | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Compounds |
CL2008001099A1 (en) * | 2007-04-19 | 2008-10-24 | Glaxo Group Ltd | COMPOUNDS DERIVED FROM INDAZOL; AND ITS USE TO TREAT DISEASES MEDIATED BY S1P1 RECEPTORS, SUCH AS MULTIPLE SCLEROSIS, AUTOIMMUNE DISEASE, INFLAMMATORY DISORDERS, DIABETES, BETWEEN OTHER. |
GB0807910D0 (en) | 2008-04-30 | 2008-06-04 | Glaxo Group Ltd | Compounds |
PT2291080E (en) | 2008-05-14 | 2015-10-30 | Scripps Research Inst | Novel modulators of sphingosine phosphate receptors |
WO2009151621A1 (en) * | 2008-06-13 | 2009-12-17 | Arena Pharmaceuticals, Inc. | Substituted (1, 2, 4-0xadiaz0l-3-yl) indolin-1-yl carboxylic acid derivatives useful as s1p1 agonists |
WO2009151626A1 (en) * | 2008-06-13 | 2009-12-17 | Arena Pharmaceuticals, Inc. | Substituted (1, 2, 4-0xadiaz0l-3-yl) indolin-1-yl carboxylic acid derivatives useful as s1p1 agonists |
WO2009153307A1 (en) | 2008-06-20 | 2009-12-23 | Glaxo Group Limited | Compounds |
EP2326621B1 (en) | 2008-07-23 | 2016-06-08 | Arena Pharmaceuticals, Inc. | SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS |
JP5878015B2 (en) * | 2008-07-23 | 2016-03-08 | ノバルティス アーゲー | Sphingosine monophosphate receptor modulators and their use to treat muscle inflammation |
RS54970B1 (en) * | 2008-08-27 | 2016-11-30 | Arena Pharm Inc | Substituted tricyclic acid derivatives as s1p1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
AU2009327133B2 (en) | 2008-12-18 | 2016-04-14 | Merck Serono S.A. | Oxadiazole fused heterocyclic derivatives useful for the treatment of multiple sclerosis |
EP2202232A1 (en) * | 2008-12-26 | 2010-06-30 | Laboratorios Almirall, S.A. | 1,2,4-oxadiazole derivatives and their therapeutic use |
EP2241558A1 (en) * | 2009-04-03 | 2010-10-20 | Merck Serono SA | Oxadiazole derivatives |
GB0910667D0 (en) * | 2009-06-19 | 2009-08-05 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
GB0910689D0 (en) * | 2009-06-19 | 2009-08-05 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
WO2011005295A1 (en) * | 2009-06-24 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Modulators of the sphingosine-1-phosphate (s1p) receptor useful for the treatment of disorders related thereto |
UA107360C2 (en) | 2009-08-05 | 2014-12-25 | Biogen Idec Inc | Bicyclic aryl sphingosine 1-phosphate analogs |
US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
EP3868377A1 (en) | 2009-11-13 | 2021-08-25 | Receptos Llc | Selective sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
EP2513095A4 (en) * | 2009-12-18 | 2013-05-15 | Glaxo Group Ltd | Oxadiazole substituted indazole derivatives for use as sphingosine 1-phosphate 1 (s1p1) receptor agonists |
EP3378854B1 (en) | 2010-01-27 | 2022-12-21 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
CA2789480A1 (en) * | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, Inc. | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
JP5735634B2 (en) | 2010-04-23 | 2015-06-17 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | 4- (5-Isoxazolyl or 5-pyrazolyl-1,2,4-oxadiazol-3-yl) -mandelic acid amide compounds as sphingosine-1-phosphate receptor 1 agonists |
WO2012040532A1 (en) | 2010-09-24 | 2012-03-29 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
UA113507C2 (en) | 2011-02-07 | 2017-02-10 | MODULATORS S1P | |
US9481659B2 (en) | 2011-05-13 | 2016-11-01 | Celgene International Ii Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
GB201202027D0 (en) * | 2012-02-06 | 2012-03-21 | Sareum Ltd | Pharmaceutical compounds |
AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
SI3310760T1 (en) | 2015-06-22 | 2023-02-28 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta(b)indol-3-yl)acetic acid for use in s1p1 receptor-associated disorders |
US11192886B2 (en) * | 2016-07-22 | 2021-12-07 | Medshine Discovery Inc. | S1P1 agonist and application thereof |
EP3518922A1 (en) | 2016-09-29 | 2019-08-07 | Celgene International II Sarl | Compounds and methods for treating lupus |
MA47503A (en) | 2017-02-16 | 2021-04-21 | Arena Pharm Inc | COMPOUNDS AND METHODS FOR THE TREATMENT OF CHRONIC INFLAMMATORY DISEASES OF THE INTESTINE WITH EXTRAINTESTINAL MANIFESTATIONS |
KR20190116416A (en) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | Compounds and Methods for Treating Primary Bile Cholangitis |
CN110627778B (en) * | 2018-06-25 | 2023-01-24 | 中国科学院上海药物研究所 | Compound containing 1,2,4-oxadiazole ring, preparation method thereof and application thereof in immunosuppressive drugs |
US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
AU2020372647A1 (en) | 2019-10-31 | 2022-06-16 | Idorsia Pharmaceuticals Ltd | Combination of a CXCR7 antagonist with an S1P1 receptor modulator |
JP2023513575A (en) * | 2020-02-11 | 2023-03-31 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | Cyclic amine compounds that are pesticidally active |
EP4212156A1 (en) | 2022-01-13 | 2023-07-19 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3939238A1 (en) | 1989-11-28 | 1991-05-29 | Bayer Ag | HETEROCYCLICALLY SUBSTITUTED ACRYLIC ACID ESTERS |
DE4002466A1 (en) | 1990-01-28 | 1991-10-10 | Bayer Ag | New pyrimidinyl-indolyl-acrylate and -acetate derivs. - useful as insecticides, acaricides, nematocides and fungicides |
US5523312A (en) | 1994-09-27 | 1996-06-04 | Sterling Winthrop Inc. | Antipicornaviral agents |
DE19620041A1 (en) | 1996-05-17 | 1998-01-29 | Merck Patent Gmbh | Adhesion receptor antagonists |
DE19643037A1 (en) | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | New oxadiazoles, processes for their preparation and their use as medicines |
JPH1180026A (en) | 1997-09-02 | 1999-03-23 | Yoshitomi Pharmaceut Ind Ltd | New immunosuppressant, its use and its identification |
EP1549640A4 (en) | 2002-06-17 | 2008-08-06 | Merck & Co Inc | 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylates and 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)pyrrolidine-3-carboxylates as edg receptor agonists |
CA2524867A1 (en) * | 2003-05-15 | 2004-12-02 | Merck & Co., Inc. | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as s1p receptor agonists |
EP1479675A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Indazole-derivatives as factor Xa inhibitors |
US20070043014A1 (en) * | 2003-10-01 | 2007-02-22 | Merck & Co., Inc. | 3,5-Aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as s1p receptor agonists |
WO2005058848A1 (en) | 2003-12-17 | 2005-06-30 | Merck & Co., Inc. | (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists |
JP5315611B2 (en) | 2004-06-23 | 2013-10-16 | 小野薬品工業株式会社 | Compound having S1P receptor binding ability and use thereof |
WO2006047195A2 (en) | 2004-10-22 | 2006-05-04 | Merck & Co., Inc. | 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as s1p receptor agonists |
JP5024039B2 (en) | 2005-02-25 | 2012-09-12 | 小野薬品工業株式会社 | Indole compounds and uses thereof |
MX2007011672A (en) | 2005-03-23 | 2007-11-15 | Actelion Pharmaceuticals Ltd | NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-l-PHOSPHATE-1 RECEPTOR AGONISTS. |
DE602006015297D1 (en) | 2005-04-22 | 2010-08-19 | Daiichi Sankyo Co Ltd | 3-AZETIDINCARBOXYLIC ACID DERIVATIVES FOR USE AS IMMUNOSUPPRESSIVA |
JP2008545767A (en) | 2005-06-08 | 2008-12-18 | ノバルティス アクチエンゲゼルシャフト | Polycyclic oxadiazoles or isoxazoles and their use as SIP receptor ligands |
AU2006283175A1 (en) | 2005-08-23 | 2007-03-01 | Irm Llc | Immunosuppressant compounds and compositions |
GB0601744D0 (en) | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic compounds |
JP2007262009A (en) | 2006-03-29 | 2007-10-11 | Dai Ichi Seiyaku Co Ltd | Heteroaryl lower carboxylic acid derivative |
BRPI0709866B8 (en) | 2006-04-03 | 2021-05-25 | Astellas Pharma Inc | hetero compounds and pharmaceutical composition comprising said compounds |
SI2069336T1 (en) | 2006-09-07 | 2013-03-29 | Actelion Pharmaceuticals Ltd. | Pyridin-4-yl derivatives as immunomodulating agents |
JO2701B1 (en) | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Compounds |
CL2008001099A1 (en) * | 2007-04-19 | 2008-10-24 | Glaxo Group Ltd | COMPOUNDS DERIVED FROM INDAZOL; AND ITS USE TO TREAT DISEASES MEDIATED BY S1P1 RECEPTORS, SUCH AS MULTIPLE SCLEROSIS, AUTOIMMUNE DISEASE, INFLAMMATORY DISORDERS, DIABETES, BETWEEN OTHER. |
-
2007
- 2007-12-17 JO JO2007554A patent/JO2701B1/en active
- 2007-12-19 MY MYPI2012004367A patent/MY156822A/en unknown
- 2007-12-19 EP EP07857808A patent/EP2091949B1/en active Active
- 2007-12-19 BR BRPI0721127-9A patent/BRPI0721127A2/en not_active IP Right Cessation
- 2007-12-19 ES ES10158582T patent/ES2389879T3/en active Active
- 2007-12-19 DK DK07857808.5T patent/DK2091949T3/en active
- 2007-12-19 KR KR1020097012841A patent/KR101495927B1/en not_active IP Right Cessation
- 2007-12-19 MY MYPI20092612A patent/MY148470A/en unknown
- 2007-12-19 SG SG2011095114A patent/SG177914A1/en unknown
- 2007-12-19 CN CN201210396720.5A patent/CN103012390B/en not_active Expired - Fee Related
- 2007-12-19 CA CA2673468A patent/CA2673468C/en not_active Expired - Fee Related
- 2007-12-19 EA EA200970612A patent/EA017406B1/en not_active IP Right Cessation
- 2007-12-19 AU AU2007336224A patent/AU2007336224B2/en not_active Ceased
- 2007-12-19 WO PCT/EP2007/064185 patent/WO2008074821A1/en active Application Filing
- 2007-12-19 DK DK10158582.6T patent/DK2206710T3/en active
- 2007-12-19 PT PT10158582T patent/PT2206710E/en unknown
- 2007-12-19 SI SI200730670T patent/SI2091949T1/en unknown
- 2007-12-19 NZ NZ577387A patent/NZ577387A/en not_active IP Right Cessation
- 2007-12-19 PL PL10158582T patent/PL2206710T3/en unknown
- 2007-12-19 PL PL07857808T patent/PL2091949T3/en unknown
- 2007-12-19 EP EP10158582A patent/EP2206710B1/en active Active
- 2007-12-19 PT PT07857808T patent/PT2091949E/en unknown
- 2007-12-19 MX MX2009006882A patent/MX2009006882A/en active IP Right Grant
- 2007-12-19 US US12/520,145 patent/US8101775B2/en not_active Expired - Fee Related
- 2007-12-19 AT AT07857808T patent/ATE509927T1/en active
- 2007-12-19 AR ARP070105729A patent/AR064452A1/en unknown
- 2007-12-19 SI SI200731001T patent/SI2206710T1/en unknown
- 2007-12-19 TW TW096148543A patent/TWI393564B/en not_active IP Right Cessation
- 2007-12-19 JP JP2009542043A patent/JP5309034B2/en not_active Expired - Fee Related
- 2007-12-20 CL CL200703755A patent/CL2007003755A1/en unknown
-
2008
- 2008-01-02 PE PE2012000146A patent/PE20121076A1/en not_active Application Discontinuation
- 2008-01-02 PE PE2008000023A patent/PE20081398A1/en not_active Application Discontinuation
-
2009
- 2009-06-04 IL IL199187A patent/IL199187A/en not_active IP Right Cessation
- 2009-06-05 DO DO2009000133A patent/DOP2009000133A/en unknown
- 2009-06-17 MA MA32003A patent/MA30999B1/en unknown
- 2009-06-23 NO NO20092385A patent/NO20092385L/en not_active Application Discontinuation
- 2009-07-13 CR CR10922A patent/CR10922A/en unknown
- 2009-10-06 HK HK10107189.4A patent/HK1140761A1/en not_active IP Right Cessation
- 2009-10-06 HK HK09109205.3A patent/HK1130255A1/en not_active IP Right Cessation
-
2011
- 2011-06-17 HR HR20110456T patent/HRP20110456T1/en unknown
- 2011-07-19 CY CY20111100700T patent/CY1111702T1/en unknown
-
2012
- 2012-08-29 HR HRP20120685TT patent/HRP20120685T1/en unknown
- 2012-09-20 CY CY20121100862T patent/CY1113131T1/en unknown
-
2014
- 2014-07-01 CR CR20140316A patent/CR20140316A/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2010513397A5 (en) | ||
JP2013519680A5 (en) | ||
JP2006518763A5 (en) | ||
HRP20110456T1 (en) | Indole derivatives as s1p1 receptor agonists | |
JP2010533722A5 (en) | ||
RU2018138707A (en) | HETEROARYL-SUBSTITUTED PYRIDINES AND METHODS OF APPLICATION | |
JP2011502958A5 (en) | ||
JP2009519965A5 (en) | ||
JP2008513515A5 (en) | ||
JP2019518036A5 (en) | ||
RU2017125365A (en) | Derivatives of azabicyclohexane as FXR agonists for use in the treatment of liver diseases and gastrointestinal diseases | |
JP2007519717A5 (en) | ||
JP2010539152A5 (en) | ||
JP2008526717A5 (en) | ||
TW200539854A (en) | Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders | |
JP2007523181A5 (en) | ||
JP2007511485A5 (en) | ||
RU2012132692A (en) | NEW S-NITROSOGLUTATHYNE REDUCTASE INHIBITORS | |
RU2013112122A (en) | NEW SUBSTITUTED QUINOLINE COMPOUNDS AS S-NITROSOGLUTATHION-REDUCTASE INHIBITORS | |
JP2020515575A5 (en) | ||
JP2014500330A5 (en) | ||
JP2014525444A5 (en) | ||
CN102816157A (en) | Nitrocatechol derivatives as COMT inhibitors | |
JP2004529174A5 (en) | ||
JP2014510132A5 (en) |